US4139479A - Textile treating composition - Google Patents
Textile treating composition Download PDFInfo
- Publication number
- US4139479A US4139479A US05/801,686 US80168677A US4139479A US 4139479 A US4139479 A US 4139479A US 80168677 A US80168677 A US 80168677A US 4139479 A US4139479 A US 4139479A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- composition according
- insoluble
- composition
- cationic surfactant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
- D06M13/473—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
- D06M13/477—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having six-membered heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
Definitions
- the invention relates to textile treatment compositions and, especially, textile softening compositions comprising cationic surfactants and certain highly insoluble carboxylates.
- the softening agents which are usually employed in compositions intended for use by the housewife are cationic surfactant compounds, commonly quaternary ammonium compounds having at least two long alkyl chains, for example distearyl dimethyl ammonium chloride.
- the positive charge on the softening compound encourages its deposition onto the fabric substrate, the surface of which is usually negatively charged.
- cationic compounds are highly effective softeners when applied in a rinse solution, there are certain disadvantages associated with their use.
- the cationic compounds having long alkyl chains are very sensitive to carry over of anionic detergent which tends to neutralize the softening effect because the anionic-cationic complex tends to precipitate out of solution.
- certain cationic surfactant compounds are expensive and in short supply and it is therefore desirable for commercial reasons, to provide softening compositions having a reduced amount of cationic surfactant compound.
- softening compositions which comprise predominantly long chain cationic compounds have the disadvantage that the treated fabrics tend to become overloaded with softener and become discolored, greasy or undesirably non-absorbent.
- the present invention provides a textile-treating composition
- a textile-treating composition comprising
- compositions are preferably intended to be formulated as aqueous dispersions for use as rinse additives, i.e., to be added to the final rinse liquor after a laundering operation.
- the compositions may be formulated so as to be suitable for spraying on to fabrics as from an aerosol container, or they may be in paste or granular form or encapsulated and in the form of a dispersion of microcapsules, or they may be releasably associated with a rigid or flexible insoluble substrate.
- R is a substituted or unsubstituted alkyl or alkenyl group having 10 to 22 carbon atoms; each R 1 is independently selected from hydrogen, (C 2 H 4 O) p H or (C 3 H 6 O) p H, where p is from 1 to 3, and C 1-3 alkyl; m is from 0 to 6; n is from 2 to 6; and A.sup.(-) represents an anion,
- substituted alkyl is intended to include alkyl groups interrupted by functional groups such as --O--, --S--, --C 6 H 4 --, etc.
- the preferred cationic surfactants of class (i) useful in the present invention are quaternary ammonium salts of the general formula
- groups R 2 and R 3 are each C 16 -C 20 alkyl and groups R 4 and R 5 are each C 1 -C 4 alkyl or hydroxyalkyl, and A is an anion, for example chloride, bromide, methyl sulfate, etc.
- Alkyl imidazolinium salts of class (iii) useful in the present invention are generally believed to have cations of the general formula ##STR2## wherein R 6 is a C 1 -C 4 alkyl radical, R 7 is C 9 -C 25 alkyl, R 8 is hydrogen or a C 8 -C 25 alkyl radical and R 9 is hydrogen or a C 1 -C 4 alkyl radical.
- a preferred member of this class is believed to have R 6 methyl and R 7 and R 8 tallow alkyl, R 9 hydrogen, and is commercially available under the trade name VARISOFT 455, marketed by Ashland Chemical Company, Ohio, U.S.A.
- Alkyl pyridinium salts of class (iv) useful in the present invention have cations of the general formula ##STR3## wherein R 10 is a C 12 -C 20 , preferably C 16 or C 18 alkyl radical.
- the main function of the cationic surfactant is to encourage deposition of softener and it is not, therefore, essential that the cationic surfactant itself have substantial softening properties, although this may be the case.
- at least a part of the cationic component of the composition comprises a surfactant having only a single alkyl chain, as such compounds have greater solubility in water and can more effectively provide the appropriate positive charge distribution and the degree of hydration on the surface of the emulsified nonionic softener particle.
- compounds of class (ii) are preferred especially those having a single C 12 -C 22 , preferably C 14 -C 18 , alkyl group.
- One group of preferred cationic surfactants of class (ii) are the quaternary ammonium salts of the formula
- group R 1 is C 12 -C 22 , preferably C 16 -C 18 fatty alkyl and groups R 2 , R 3 and R 4 are each C 1 -C 4 alkyl, preferably methyl.
- Another group of useful surfactants of class (ii) are the mono-amine salts of the formula R 1 R 2 R 3 N + H A - where R 1 is C 12 -C 22 , preferably C 16 -C 18 alkyl and R 2 and R 3 are each selected independently from hydrogen and C 1 -C 4 alkyl, especially methyl.
- the polyamine salts of this type provide additional positive charge to the particle and thereby improve deposition of the heavy metal soaps.
- the mono substituted derivatives of 1,3-diaminopropanol are very effective, that is compounds of the formula ##STR5## wherein R is as described above, and preferably is predominantly C 16 -C 18 alkyl, derived from tallow fatty acids.
- a - may represent a dihalide or any appropriate acidic radical such as the diacetate, or higher saturated or unsaturated acyl groups up to C 22 .
- a preferred compound of this class is believed to have the formula ##STR6## and is sold under the trade names Dinoramac (Messrs. Pierrefitte-Auby) or Duomac (Messrs. Armour-Hess), or more preferably the corresponding halide, especially chloride.
- "Tallowyl" represents the predominantly C 16 to C 18 alkyl groups derived from tallow fatty acids.
- the unprotonated amine may also be used to prepare the compositions but it is highly preferred for a good product performance that their pH be such that at least one of the amine groups of the polyamine is present in them, or at least in the treatment bath, in protonated form.
- N-tallow-N,N,N', N', N' pentamethyl-1,3 propylene diammonium dichloride which is commercially available under the trade names STABIRAN MS-3 (Pierrefitte-Auby), DUOMAC (Armour-Hess); and ADOGEN 477 (Ashland Co.), and N-tallow-N,N',N'-triethanol-1,3-propylenediamine hydrochloride.
- Highly preferred diamines are compounds carrying ethoxylate groups on the nitrogen atoms, for example those having the general formula ##STR7##
- the water insoluble carboxylates should preferably be highly insoluble, that is they should have water solubility less than 20 g. per liter at 25° C., preferably less than 1 g. per liter.
- Preferred carboxylates are the heavy metal salts of fatty acids (whether derived from natural fats or synthetically, and whether saturated or unsaturated) having about 16 to 24 carbon atoms. Suitable acids include palmitic, oleic, linoleic, stearic, arachidic, behenic, and the like. Suitable metals include calcium, magnesium, aluminium, zinc, barium and others, with preference for those whose carboxylates are uncoloured. The mono, di, and where applicable, tri-carboxylates may be employed. Preferred are calcium distearate and aluminium distearate.
- the proportions of cationic surfactant and insoluble carboxylate in the compositions can vary quite widely.
- the relative proportions of cationic and carboxylate can be from about 50:1 to about 1:10, preferably from about 10:1 to 2:3, and especially from about 3:2 to 2:3.
- concentration of these components in the compositions of the invention depends upon the extent to which they are designed to be diluted in a treatment bath or solution. Rinse additive compositions used at low concentrations have become widely employed in recent years and the amount to be used has become conventional.
- a concentration about 0.1 to 15% cationic surfactant preferably from about 2 to 10% by weight is appropriate, and from about 0.1 to 10%, preferably about 1 to 6% of insoluble carboxylate.
- concentration of about 10 to 25 parts per million to 0.1%, preferably about 50 to 500 ppm by weight of heavy metal carboxylate and cationic together may be employed. Higher concentrations might be used in compositions intended to be sprayed neat onto fabrics.
- the compositions may contain small amounts of nonionic surfactants as emulsifiers.
- they may contain nonionic components, not necessarily surfactants, having beneficial effects upon the fabrics to be treated or in the ironing operation.
- Preferred nonionic fabric conditioning substances are textile softeners represented by fatty acid esters and partial esters of mono- or polyhydric alcohols having from 1 to 8 carbon atoms. It is preferred that the fatty acid ester should have at least 1 free, i.e., unesterified, hydroxyl group and at least one fatty acyl group.
- Such additives include nonionic textile softening agents such as sorbitan esters, as described in German Offenlegungsschrift 2,516,104, glyceryde esters of C 12 -C 22 fatty acids, e.g., glycerylmonostearate, and fatty alkyl esters of C 2 -C 6 polyols, and zwitterionic surfactants or amine or phosphine oxides as described in U.S. Pat. No. 3,686,025.
- Other substances which may be added are pyrodextrins and modified dextrins.
- a content of about 1 to about 10% by weight, preferably about 1.5 to about 6% of said agents is usually suitable.
- compositions may contain other textile treatment or conditioning agents.
- agents include silicones.
- Some suitable silicones are predominantly linear polymers, that is they are poly dialkyl- or diaryl-siloxanes.
- the alkyl groups have 1 to 5 carbon atoms, and are preferably methyl.
- the alkyl groups may be wholly or partially fluorinated. A limited degree of cross linking can be tolerated, and up to about 10% by weight of mono-alkyl siloxanes may be present in the silicones.
- silicones are polydimethyl siloxanes having viscosity at 25° C. in the range 100 to 200000 centistockes, preferably 1000 to 120000.
- Other preferred silicones are fluorinated silicones having viscosity at 25° C. of at least 100 centistokes, as described in German Offenlegungsschrift No. 2,631,419.
- Preferred are silicones of cationic character. These silicones are either:
- the silicone component is preferably used in an amount of from about 0.5% to about 10%, most preferably from 1% to 6% of the softener composition.
- the ratio of cationic surfactant to total of insoluble soap and additional component is usually in the range from about 10:1 to 1:10.
- compositions being formulated may also be present.
- Such components are preservatives, bactericides, whether effective to protect the composition or to treat fabrics, viscosity controllers, coloring and perfuming materials and the like.
- the components may be simply mixed into the aqueous medium optionally with small amounts of nonionic surfactants, or lower alcohols.
- the insoluble carboxylate is mixed first into molten cationic surfactant, optionally together with other conditioning agents mentioned above, and this mixture dispersed in the aqueous medium.
- a composition was prepared by dispersing of 5.9% by weight of molten ditallow dimethyl ammonium chloride (DTDMAC) and 2% aluminium distearate in water. Fabrics steeped in a dilute aqueous solution of the composition and dried were found to be softer than fabrics treated with a similar composition containing no distearate, and as soft as fabric treated with a composition comprising 8.0% DTDMAC in water.
- DTDMAC molten ditallow dimethyl ammonium chloride
- a composition was prepared consisting of a dispersion of 4% by weight of tallowyl propylene diamine hydrochloride, and 3.5% of calcium distearate in water. Fabrics steeped in a dilute aqueous solution of the composition and dried were found to be as soft as fabrics treated with a similar composition comprising 5.9% DTDMAC and softer than those treated with a composition comprising 8.8% tallowyl propylene diamine hydrochloride.
- compositions were prepared consisting of dispersions in water of, by weight:
- a textile treatment composition is prepared by dispersing a melt of the following components in 92 parts (%) by weight of water
- the glycerine monostearate may be replaced by sorbitan monostearate, ethylene glycol monostearate, diglycerol monotallowate, xylitol monopalmitate, or a 1:2 molar mixture of glycerine tristearate and monostearate.
- a textile treatment composition was prepared by mixing a melt of 9 part VARISOFT 455 (Imidazolinium textile softener marketed by Ashland Chemical Co.) and 1 part aluminium distearate in 90 parts of water.
- composition is an effective textile softener when employed as a dilute aqueous solution.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB23176/76 | 1976-06-04 | ||
GB2317676A GB1576326A (en) | 1976-06-04 | 1976-06-04 | Textile treating compositions |
GB45079/76 | 1976-10-09 | ||
GB4507976 | 1976-10-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
US4139479A true US4139479A (en) | 1979-02-13 |
Family
ID=26256387
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/801,686 Expired - Lifetime US4139479A (en) | 1976-06-04 | 1977-05-31 | Textile treating composition |
Country Status (11)
Country | Link |
---|---|
US (1) | US4139479A (nl) |
JP (1) | JPS5319497A (nl) |
AT (1) | AT381963B (nl) |
BE (1) | BE855418A (nl) |
CA (1) | CA1090056A (nl) |
CH (1) | CH627214A5 (nl) |
DE (1) | DE2724821A1 (nl) |
ES (1) | ES459456A1 (nl) |
FR (1) | FR2353632A1 (nl) |
IT (1) | IT1077225B (nl) |
NL (1) | NL190078C (nl) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4296174A (en) * | 1980-08-08 | 1981-10-20 | E. I. Du Pont De Nemours And Company | Spandex filaments containing certain metallic soaps |
US4313895A (en) * | 1980-06-24 | 1982-02-02 | Akzona Incorporated | Alkoxylated diquaternary ammonium compounds |
EP0065387A1 (en) * | 1981-05-08 | 1982-11-24 | Unilever Plc | Fabric conditioning materials |
US4370026A (en) * | 1979-09-10 | 1983-01-25 | Thomson-Csf | Illuminating device for providing an illumination beam with adjustable distribution of intensity and a pattern-transfer system comprising such a device |
US4436637A (en) | 1982-12-13 | 1984-03-13 | Colgate-Palmolive Company | Fabric softening heavy duty liquid detergent containing a mixture of water insoluble soap and clay |
US4460485A (en) * | 1983-07-15 | 1984-07-17 | Lever Brothers Company | Polyester fabric conditioning and whitening composition |
AT387787B (de) * | 1982-12-13 | 1989-03-10 | Colgate Palmolive Co | Textilweichmachende waschmittelmischung sowie weichmacher fuer eine waschmittelmischung, und verfahren zur deren herstellung |
US4971706A (en) * | 1986-08-04 | 1990-11-20 | Wixon Harold E | Fabric softening composition |
US20050022313A1 (en) * | 2003-07-08 | 2005-02-03 | Scheidler Karl J. | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
US20070085050A1 (en) * | 2003-07-08 | 2007-04-19 | Scheidler Karl J | Methods and Compositions for Improving Light-Fade Resistance and Soil Repellency of Textiles and Leathers |
WO2024054520A1 (en) * | 2022-09-07 | 2024-03-14 | Kao Corporation | Stable amine-based defoamer for admixture additives |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3920563A (en) * | 1972-10-31 | 1975-11-18 | Colgate Palmolive Co | Soap-cationic combinations as rinse cycle softeners |
US3958059A (en) * | 1973-10-01 | 1976-05-18 | The Procter & Gamble Company | Fabric treatment composition |
US3959155A (en) * | 1973-10-01 | 1976-05-25 | The Procter & Gamble Company | Detergent composition |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1368540A (en) * | 1972-04-11 | 1974-09-25 | Unilever Ltd | Rinse-wax formulation |
-
1977
- 1977-05-27 CA CA279,332A patent/CA1090056A/en not_active Expired
- 1977-05-31 US US05/801,686 patent/US4139479A/en not_active Expired - Lifetime
- 1977-06-02 DE DE19772724821 patent/DE2724821A1/de active Granted
- 1977-06-03 CH CH687477A patent/CH627214A5/de not_active IP Right Cessation
- 1977-06-03 ES ES77459456A patent/ES459456A1/es not_active Expired
- 1977-06-03 IT IT7724377A patent/IT1077225B/it active
- 1977-06-03 FR FR7717156A patent/FR2353632A1/fr active Granted
- 1977-06-03 AT AT0396577A patent/AT381963B/de not_active IP Right Cessation
- 1977-06-03 NL NLAANVRAGE7706120,A patent/NL190078C/nl not_active IP Right Cessation
- 1977-06-04 JP JP6621277A patent/JPS5319497A/ja active Pending
- 1977-06-06 BE BE178219A patent/BE855418A/nl not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3920563A (en) * | 1972-10-31 | 1975-11-18 | Colgate Palmolive Co | Soap-cationic combinations as rinse cycle softeners |
US3958059A (en) * | 1973-10-01 | 1976-05-18 | The Procter & Gamble Company | Fabric treatment composition |
US3959155A (en) * | 1973-10-01 | 1976-05-25 | The Procter & Gamble Company | Detergent composition |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4370026A (en) * | 1979-09-10 | 1983-01-25 | Thomson-Csf | Illuminating device for providing an illumination beam with adjustable distribution of intensity and a pattern-transfer system comprising such a device |
US4313895A (en) * | 1980-06-24 | 1982-02-02 | Akzona Incorporated | Alkoxylated diquaternary ammonium compounds |
US4296174A (en) * | 1980-08-08 | 1981-10-20 | E. I. Du Pont De Nemours And Company | Spandex filaments containing certain metallic soaps |
EP0065387A1 (en) * | 1981-05-08 | 1982-11-24 | Unilever Plc | Fabric conditioning materials |
US4427558A (en) | 1981-05-08 | 1984-01-24 | Lever Brothers Company | Fabric conditioning materials |
AT387787B (de) * | 1982-12-13 | 1989-03-10 | Colgate Palmolive Co | Textilweichmachende waschmittelmischung sowie weichmacher fuer eine waschmittelmischung, und verfahren zur deren herstellung |
US4436637A (en) | 1982-12-13 | 1984-03-13 | Colgate-Palmolive Company | Fabric softening heavy duty liquid detergent containing a mixture of water insoluble soap and clay |
AT387788B (de) * | 1982-12-13 | 1989-03-10 | Colgate Palmolive Co | Fluessiges, gewebeweichmachendes vollwaschmittel |
US4460485A (en) * | 1983-07-15 | 1984-07-17 | Lever Brothers Company | Polyester fabric conditioning and whitening composition |
US4971706A (en) * | 1986-08-04 | 1990-11-20 | Wixon Harold E | Fabric softening composition |
US20050022313A1 (en) * | 2003-07-08 | 2005-02-03 | Scheidler Karl J. | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
US7157018B2 (en) | 2003-07-08 | 2007-01-02 | Scheidler Karl J | Compositions for improving the light-fade resistance and soil repellancy of textiles and leathers |
US20070085050A1 (en) * | 2003-07-08 | 2007-04-19 | Scheidler Karl J | Methods and Compositions for Improving Light-Fade Resistance and Soil Repellency of Textiles and Leathers |
US7824566B2 (en) | 2003-07-08 | 2010-11-02 | Scheidler Karl J | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
WO2024054520A1 (en) * | 2022-09-07 | 2024-03-14 | Kao Corporation | Stable amine-based defoamer for admixture additives |
Also Published As
Publication number | Publication date |
---|---|
NL7706120A (nl) | 1977-12-06 |
JPS5319497A (en) | 1978-02-22 |
DE2724821C2 (nl) | 1989-04-06 |
ES459456A1 (es) | 1978-11-16 |
IT1077225B (it) | 1985-05-04 |
CH627214A5 (nl) | 1981-12-31 |
NL190078B (nl) | 1993-05-17 |
FR2353632B1 (nl) | 1982-03-26 |
NL190078C (nl) | 1993-10-18 |
ATA396577A (de) | 1986-05-15 |
CA1090056A (en) | 1980-11-25 |
AT381963B (de) | 1986-12-29 |
FR2353632A1 (fr) | 1977-12-30 |
BE855418A (nl) | 1977-12-06 |
DE2724821A1 (de) | 1977-12-15 |
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